Abstract
Hyaluronic acid (HA) is a natural polysaccharide with great biocompatibility for a variety of biomedical applications, such as tissue scaffolds, dermal fillers, and drug-delivery carriers. Despite the medical impact of HA, its poor adhesiveness and short-term in vivo stability limit its therapeutic efficacy. To overcome these shortcomings, a versatile modification strategy for the HA backbone has been developed. This strategy involves tethering phenol moieties on HA to provide both robust adhesiveness and intermolecular cohesion and can be used for oxidative crosslinking of the polymeric chain. However, a lack of knowledge still exists regarding the interchangeable phenolic adhesion and cohesion depending on the type of oxidizing agent used. Here, we reveal the correlation between phenolic adhesion and cohesion upon gelation of two different HA–phenol conjugates, HA–tyramine and HA–catechol, depending on the oxidant. For covalent/non-covalent crosslinking of HA, oxidizing agents, horseradish peroxidase/hydrogen peroxide, chemical oxidants (e.g., base, sodium periodate), and metal ions, were utilized. As a result, HA–catechol showed stronger adhesion properties, whereas HA–tyramine showed higher cohesion properties. In addition, covalent bonds allowed better adhesion compared to that of non-covalent bonds. Our findings are promising for designing adhesive and mechanically robust biomaterials based on phenol chemistry.
Highlights
Hyaluronic acid (HA) is a natural polysaccharide constructed from two alternating units of N-acetyl-D-glucosamine and D-glucuronic acid [1,2]
Of catechol was 3.7%, which was calculated by integral values of protons in aromatic rings of catechol compared to protons of HA backbone in 1H NMR spectra
When the catechol is tethered on polysaccharide, a few free catechol derivatives can be intercalated among the polymeric chains due to their intrinsic adhesiveness [24]
Summary
Hyaluronic acid (HA) is a natural polysaccharide constructed from two alternating units of N-acetyl-D-glucosamine and D-glucuronic acid [1,2]. Previous research has further shown that HA is very versatile in its use in medical treatment and tissue engineering because of its high biocompatibility, biodegradability, viscoelasticity, and non-toxic characteristics [5,6]. These properties make HA an ideal biomaterial for injectable hydrogels, wound patches, 3D bioprinting, tissue scaffolds, and drug delivery [7,8,9,10,11]. Adhesive properties enable the research to be conducted in the past few years to develop an adhesive HA-derived hydrogel for medical treatment [20]
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